Artifactory plugin is using the entire artifact file system path when attempting to deploy the artifact from a freestyle job using Job configuration File Spec. I believe the cause of the issue was upgrading Jenkins to 2.89.4 from 2.73.3, as this job has been working successfully before the upgrade (but I also upgraded plugins, not sure Artifactory plugin's dependencies).

File spec looks like so:

{
"files": [
{
"pattern": "${WORKSPACE}/App-${App_Version}.zip",
"target": "my-repo/App/${App_Version}/",
"recursive": "true",
"flat" : "false"
}
]
}

The artifact is properly identified in the job when run, but when it goes to deploy it uses the entire C:\ file system path in the URL. Log output looks like:

For pattern: C:/Jenkins/jobs/app/workspace/app-version-1.6.11.zip 1 artifacts were found.
Deploying artifact: https://server.com/artifactory/repos/app/1.6.11/C%3A/Jenkins/jobs/app/workspace/app-version-1.6.11.zip
ERROR: Failed to deploy file. Status code: 500 Response message: Artifactory returned the following errors:
Invalid path. ':' is not a valid name character: repos/app/1.6.11/C:/ Status code: 500
java.io.IOException: Failed to deploy file. Status code: 500 Response message: Artifactory returned the following errors:
Invalid path. ':' is not a valid name character: repos/app/1.6.11/C:/ Status code: 500
at org.jfrog.build.extractor.clientConfiguration.client.ArtifactoryBuildInfoClient.uploadFile(ArtifactoryBuildInfoClient.java:656)
at org.jfrog.build.extractor.clientConfiguration.client.ArtifactoryBuildInfoClient.deployArtifact(ArtifactoryBuildInfoClient.java:343)
at org.jfrog.build.extractor.clientConfiguration.util.spec.SpecsHelper.deploy(SpecsHelper.java:291)
at org.jfrog.build.extractor.clientConfiguration.util.spec.SpecsHelper.uploadArtifactsBySpec(SpecsHelper.java:65)
at org.jfrog.hudson.generic.GenericArtifactsDeployer$FilesDeployerCallable.invoke(GenericArtifactsDeployer.java:189)
at org.jfrog.hudson.generic.GenericArtifactsDeployer$FilesDeployerCallable.invoke(GenericArtifactsDeployer.java:130)
at hudson.FilePath.act(FilePath.java:997)
at hudson.FilePath.act(FilePath.java:975)
at org.jfrog.hudson.generic.GenericArtifactsDeployer.deploy(GenericArtifactsDeployer.java:76)
at org.jfrog.hudson.generic.ArtifactoryGenericConfigurator$1.tearDown(ArtifactoryGenericConfigurator.java:401)
at hudson.model.Build$BuildExecution.doRun(Build.java:174)
at hudson.model.AbstractBuild$AbstractBuildExecution.run(AbstractBuild.java:504)
at hudson.model.Run.execute(Run.java:1724)
at hudson.model.FreeStyleBuild.run(FreeStyleBuild.java:43)
at hudson.model.ResourceController.execute(ResourceController.java:97)
at hudson.model.Executor.run(Executor.java:429)
Finished: FAILURE

It is failing due to the : character in C:\, but regardless it should not be trying to deploy to that URL. Before the 2.89.4 upgrade it was working fine, now broken with no changed to the job config.